DE1445186C3 - 3,3'-di-2-imidazolin-2-yl-carbanilide - Google Patents

3,3'-di-2-imidazolin-2-yl-carbanilide

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Publication number
DE1445186C3
DE1445186C3 DE1445186A DE1445186A DE1445186C3 DE 1445186 C3 DE1445186 C3 DE 1445186C3 DE 1445186 A DE1445186 A DE 1445186A DE 1445186 A DE1445186 A DE 1445186A DE 1445186 C3 DE1445186 C3 DE 1445186C3
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Germany
Prior art keywords
carbanilide
imidazolin
washed
acid
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
DE1445186A
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German (de)
Other versions
DE1445186B2 (en
DE1445186A1 (en
Inventor
Rudolf Dr. Kehrsatz Fischer
Rudolf Dr. Muri Bern Hirt
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Wander AG
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Wander AG
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Publication of DE1445186A1 publication Critical patent/DE1445186A1/en
Publication of DE1445186B2 publication Critical patent/DE1445186B2/en
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Publication of DE1445186C3 publication Critical patent/DE1445186C3/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/40—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D233/24—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/44—Nitrogen atoms not forming part of a nitro radical
    • C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/14—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings

Description

a) 2-(3-Aminophenyl)-imidazolin der Formela) 2- (3-aminophenyl) imidazoline of the formula

N^ ^x N ^ ^ x

(II) HN'(II) HN '

in an sich bekannter Weise mit Kohlensäure oder Phosgen umsetzt, oder b) eine Verbindung der allgemeinen Formelreacts in a manner known per se with carbonic acid or phosgene, or b) a compound of the general formula

Alkyl—O Ο—AlkylAlkyl-O Ο-alkyl

C—f V-NH-CO —NH-ff \-C (III) C — f V-NH-CO —NH-ff \ -C (III)

^x)^ x) KJ x KJ x

HN V' V^ NHHN V 'V ^ NH

in an sich bekannter Weise mit Äthylendiamin umsetzt, worauf man gewünschtenfalls die erhaltene freie Base mit einer physiologisch annehmbaren Säure in ein Salz überführt.Reacts in a known manner with ethylenediamine, whereupon, if desired, the obtained free Base converted into a salt with a physiologically acceptable acid.

3. Arzneimittel, bestehend aus 3,3'-Di-2-imidazolin-2-yl-carbanilid oder dessen Salzen mit physiologisch annehmbaren Säuren und üblichen Träger- oder Verdünnungsmitteln.3. Medicines consisting of 3,3'-di-2-imidazolin-2-yl-carbanilide or its salts with physiological acceptable acids and common carriers or diluents.

Gegenstand der Erfindung ist 3,3'-Di-2-imidazolin-2-yl-carbanilid der FormelThe invention relates to 3,3'-di-2-imidazolin-2-yl-carbanilide of the formula

nhnh

sowie dessen Salze mit physiologisch annehmbaren Säuren.and its salts with physiologically acceptable acids.

Das 3,3'-Di-2-imidazolin-2-yl-carbanilid der Formel I erhält man, indem man entweder 2-(3-Aminophenyl)-imidazolin der Formel :;,The 3,3'-di-2-imidazolin-2-yl-carbanilide of the formula I are obtained either by 2- (3-aminophenyl) imidazoline of the formula:; ,

Nx κ\Nx κ \

V-f Y- NH, (II)V-f Y- NH, (II)

in an sich bekannter Weise mit Kohlensäure oder Phosgen umsetzt, oder b) eine Verbindung der allgemeinen Formel ■ . ■-. . , ■ ·"-. -. . · . ■ . · .. Reacts in a manner known per se with carbonic acid or phosgene, or b) a compound of the general formula ■. ■ -. . , ■ · "-. -.. ·. ■. · ..

• Alkyl—O -■-■■■■■·'■ Ο—Alkyl .• Alkyl — O - ■ - ■■■■■ · '■ Ο — alkyl.

C HN v ^ NHC HN v ^ NH

in an sich bekannter Weise mit Äthylendiamin um- in ein Salz überführt. Als mögliches Salz sei dasjenige setzt, worauf man gewünschtenfalls die erhaltene der Salzsäure erwähnt.converted into a salt in a manner known per se with ethylenediamine. Let that be the possible salt sets, whereupon the hydrochloric acid obtained is mentioned, if desired.

freie Base mit einer physiologisch annehmbaren Säure 3,3'-Di-2-imidazolin-2-yl-carbanilid sowie seinefree base with a physiologically acceptable acid 3,3'-di-2-imidazolin-2-yl-carbanilide as well as his

Salze mit physiologisch annehmbaren Säuren sind neue Verbindungen, die sich auf Grund ihrer pharmakodynamischen Wirkungen, vor allem als Chemotherapeutika, insbesondere zur Behandlung von mit Babesien infizierten Tieren eignen.Salts with physiologically acceptable acids are new compounds that differ due to their pharmacodynamic Effects, especially suitable as chemotherapeutic agents, especially for the treatment of animals infected with Babesia.

Es ist bekannt, daß 3,3'-Diamidino-carbanilid und seine Säure-Additionssalze wirksam sind bei der Bekämpfung von Infektionen am Tier, welche durch Protozoen der Babesien-Familie, wie Babesia rodhaini, verursacht wurden (vgl. australische Patentschrift 244912 oder belgische Patentschrift 585 595).It is known that 3,3'-diamidino-carbanilide and its acid addition salts are effective in combating of infections in animals caused by protozoa of the Babesia family, such as Babesia rodhaini, caused (see Australian patent specification 244912 or Belgian patent specification 585 595).

Es wurde nun überraschend gefunden, daß das erfindungsgemäße 3,3'-Di-2-imidazolin-2-yl-carbanilid an Mäusen und Ratten wesentlich wirksamer ist gegen Babesia rodhaini als das vorbekannte 3,3'-Diamidinocarbanilid. Zudem zeigt das erfindungsgemäße Produkt eine größere therapeutische Breite (vgl. Elizabeth Beveridge, Res. vet. Sei., 1969, 10, 534 und Gisela S c h m i d t et al, Res. vet. Sei., 1969, 10, 530).It has now surprisingly been found that the 3,3'-di-2-imidazolin-2-yl-carbanilide according to the invention in mice and rats is much more effective against Babesia rodhaini than the previously known 3,3'-diamidinocarbanilide. In addition, the product according to the invention shows a greater therapeutic range (cf. Elizabeth Beveridge, Res. Vet. Sci., 1969, 10, 534 and Gisela S c h m i d t et al, Res. Vet. Sci., 1969, 10, 530).

Beispiel 1example 1

15 g 2-(3-Aminophenyl)-imidazolin-dihydrochlorid und 30 g Natriumacetat werden in 150 ml Wasser gelöst. In die Lösung wird unter gutem Rühren Phosgen eingeleitet, bis die Diazo-Probe negativ ist. Die ge- 2S bildete Base wird mit Natronlauge freigelegt, zerstoßen und abgenutscht. Der Rückstand wird mit Wasser gewaschen und in verdünnter Essigsäure gelöst. Die Lösung wird mit Kohle geklärt, mit konzentrierter Salzsäure versetzt und mit Luftkristallen von 3,3'-Diimidazolin-2-yl-carbanilid-dihydrochlorid versetzt. Es scheiden sich Kristalle ab, welche nach Kühlung auf 00C abgenutscht, fünfmal mit 10%iger Salzsäure und dann mit Alkohol und Äther gewaschen werden. Nach Trocknen am Vakuum bei 50° C erhält man 15g15 g of 2- (3-aminophenyl) imidazoline dihydrochloride and 30 g of sodium acetate are dissolved in 150 ml of water. Phosgene is passed into the solution with thorough stirring until the diazo sample is negative. The total 2 S formed base is exposed, crushed and filtered with suction with sodium hydroxide. The residue is washed with water and dissolved in dilute acetic acid. The solution is clarified with charcoal, concentrated hydrochloric acid and air crystals of 3,3'-diimidazolin-2-ylcarbanilide dihydrochloride are added. It separate out crystals, which are washed by suction filtration after cooling to 0 0 C, washed five times with 10% hydrochloric acid and then with alcohol and ether. After drying in vacuo at 50 ° C., 15 g are obtained

20 3,3'-Di-2-imidazolin-2-yl-carbanilid-dihydrochlorid vom Schmelzpunkt 3500C (unter Zersetzung). 20 3,3'-Di-2-imidazolin-2-yl-carbanilide dihydrochloride of melting point 350 0 C (with decomposition).

Beispiel 2Example 2

43 g N,N'-Di-(m-äthoxy-carbonimidophenyl)-harnstoff werden in 150 ml absolutem Äthanol gelöst. Hierauf gibt man 20 ml Äthylendiamin zu und erhitzt während 8 Stunden auf 60 bis 700C. Der nach Eindampfen des Reaktionsgemisches erhaltene Rückstand wird in 100 ml Wasser gelöst, und die wäßrige Lösung wird mit einem Überschuß an Sodalösung versetzt. Das ausgeschiedene basische Produkt wird abgenutscht, mit Wasser gewaschen und in verdünnter Essigsäure gelöst. Die essigsaure Lösung wird mit Kohle geklärt und mit einem Überschuß an Salzsäure versetzt. Man kühlt auf 0° C ab, nutscht das abgeschiedene Hydrochlorid ab und wäscht es erst mit 10%iger Salzsäure und dann mit Äthanol und Äther. Nach dem Trocknen erhält man 36 g 3,3'-Di-2-imidazolin-2-yl-carbanilid-dihydrochlorid vom Zersetzungsprodukt 3500C.43 g of N, N'-di (m-ethoxy-carbonimidophenyl) -urea are dissolved in 150 ml of absolute ethanol. Thereupon was added 20 ml ethylene diamine and the mixture heated for 8 hours at 60 to 70 0 C. The residue obtained after evaporation of the reaction mixture is dissolved in 100 ml of water, and the aqueous solution is treated with an excess of sodium carbonate solution. The precipitated basic product is filtered off with suction, washed with water and dissolved in dilute acetic acid. The acetic acid solution is clarified with charcoal and mixed with an excess of hydrochloric acid. It is cooled to 0 ° C., the precipitated hydrochloride is filtered off with suction and washed first with 10% hydrochloric acid and then with ethanol and ether. After drying, 36 g of 3,3'-di-2-imidazolin-2-yl-carbanilide dihydrochloride from the decomposition product 350 0 C.

Den in diesem Beispiel verwendeten Ausgangsstoff erhält man wie folgt:The raw material used in this example is obtained as follows:

Zu einer Suspension von 26,2 g N,N'-Di-(m-cyanophenyl)-harnstoff in 300 ml wasserfreiem Chloroform gibt man 50 ml wasserfreies, mit Chlorwasserstoffgas gesättigtes Äthanol und läßt während 5 Tagen bei Zimmertemperatur stehen. Das entstandene Kristallisat wird abgenutscht, mit wasserfreiem Äther gewaschen und getrocknet. Man erhält 43 g Ν,Ν'-Di-(m-Äthoxy-carbonimido-phenyl)-harnstoff, welcher direkt und ohne weitere Reinigung weiterverwendet wird.To a suspension of 26.2 g of N, N'-di (m-cyanophenyl) urea in 300 ml of anhydrous chloroform 50 ml of anhydrous ethanol, saturated with hydrogen chloride gas, are added and left for 5 days Stand at room temperature. The resulting crystals are filtered off with suction and washed with anhydrous ether and dried. 43 g of Ν, Ν'-di (m-ethoxy-carbonimido-phenyl) -urea are obtained, which is used directly and without further purification.

Für diese Arbeitsweise wird Patentschutz hier nicht begehrt.Patent protection is not sought for this way of working.

Claims (2)

1 21 2 Patentansprüche:
3.3 -Di^-imidazolin^-yl-carbanilid der Formel IPatent claims:
3.3 -Di ^ -imidazolin ^ -yl-carbanilide of the formula I. ^ NH- CO — NH-/V-/ I (D^ NH- CO - NH- / V- / I (D V XNHJ V X NH J sowie dessen Salze mit physiologisch annehmbaren Säuren.and its salts with physiologically acceptable acids. 2. Verfahren zur Herstellung von 3,3'-Di-2-imidazolin-2-yl-carbaniIid, dadurch gekennzeichnet, daß man entweder ·".:.'2. Process for the preparation of 3,3'-di-2-imidazolin-2-yl-carbaniIid, characterized in that one either ·".:.'
DE1445186A 1960-10-14 1961-10-02 3,3'-di-2-imidazolin-2-yl-carbanilide Expired DE1445186C3 (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
CH1154760 1960-10-14
CH261761 1961-03-03
CH305961 1961-03-14
CH391961 1961-04-04
CH496661 1961-04-28
CH720161 1961-06-20

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DE1445186A1 DE1445186A1 (en) 1968-10-24
DE1445186B2 DE1445186B2 (en) 1974-03-28
DE1445186C3 true DE1445186C3 (en) 1974-11-07

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US (1) US3338917A (en)
DE (1) DE1445186C3 (en)
DK (1) DK119352B (en)
FR (1) FR1464M (en)
GB (1) GB1007334A (en)
MX (1) MX3465E (en)
NL (1) NL139886B (en)
NO (1) NO119949B (en)
OA (1) OA01084A (en)
SE (2) SE329151B (en)

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Publication number Priority date Publication date Assignee Title
BE757956A (en) * 1969-10-24 1971-04-23 Ici Ltd ANTIVIRAL COMPOUNDS
BE757955A (en) * 1969-10-24 1971-04-23 Ici Ltd ANTIVIRAL COMPOSITIONS
WO1995032945A1 (en) * 1994-06-01 1995-12-07 Arris Pharmaceutical Corporation Compositions and methods for treating mast-cell mediated conditions
US5633388A (en) * 1996-03-29 1997-05-27 Viropharma Incorporated Compounds, compositions and methods for treatment of hepatitis C
US20040087798A1 (en) * 2000-03-14 2004-05-06 Akira Yamada Novel amide compounds
US6949567B2 (en) 2001-02-26 2005-09-27 4Sc Ag Compounds for the treatment of protozoal diseases
CN100390150C (en) * 2006-06-05 2008-05-28 吴汝林 Method for preparing imidazophenylurea hydrochloride
EP2446074A1 (en) 2009-06-25 2012-05-02 Texas Research International, Inc. Novel polyurea fiber
CN102898375B (en) * 2012-11-13 2015-07-22 齐鲁动物保健品有限公司 Preparation method of 2-(3-aminophenyl) imidazoline hydrochloride
WO2014089226A1 (en) * 2012-12-04 2014-06-12 The Board Of Trustees Of The University Of Illinois Antibacterial compounds targeting isoprenoid biosynthesis
CN103896843B (en) * 2014-04-17 2016-02-24 山东久隆精细化工有限公司 A kind of preparation method of imidazophenylurea
TWI825331B (en) * 2019-07-12 2023-12-11 日商日本化藥股份有限公司 Luminescent compound or salt thereof, and polarizing luminescent element, polarizing luminescent plate, and display comprising the same
WO2022249192A1 (en) * 2021-05-27 2022-12-01 Ramot At Tel-Aviv University Ltd. Broad-spectrum metastasis suppressing compounds and therapeutic uses thereof in human tumors

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US2473577A (en) * 1945-05-28 1949-06-21 Petrolite Corp Carbonic acid amides of certain substituted glyoxalidines

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SE335975B (en) 1971-06-21
FR1464M (en) 1962-08-27
NO119949B (en) 1970-08-03
SE329151B (en) 1970-10-05
GB1007334A (en) 1965-10-13
DK119352B (en) 1970-12-21
DE1445186B2 (en) 1974-03-28
MX3465E (en) 1980-09-12
NL139886B (en) 1973-10-15
US3338917A (en) 1967-08-29
OA01084A (en) 1968-08-07
DE1445186A1 (en) 1968-10-24

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SH Request for examination between 03.10.1968 and 22.04.1971
C3 Grant after two publication steps (3rd publication)
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EHJ Ceased/non-payment of the annual fee